Rongalite-Induced Transition-Metal and Hydride-Free Reductive Aldol Reaction: A Rapid access to 3,3´- Disubstituted Oxindoles and Its Mechanistic Studies

2022 ◽  
Author(s):  
Sivaparwathi Golla ◽  
Naveenkumar Anugu ◽  
Swathi Jalagam ◽  
Hari Prasad Kokatla
Keyword(s):  
Transition Metal ◽  
Aldol Reaction ◽  
Dual Role ◽  
Biologically Active ◽  
Mechanistic Studies ◽  
Rapid Access ◽  
Reductive Aldol ◽  
Isatin Derivatives

A transition-metal and hydride-free reductive aldol reaction has been developed for the synthesis of biologically active 3,3´-disubstituted oxindoles from isatin-derivatives using rongalite. In this protocol, rongalite plays the dual role...

A REVIEW ON RECENT ADVANCES IN CHEMISTRY, SYNTHESIS AND BIOLOGICAL APPLICATIONS OF ISATIN DERIVATIVES

2018 ◽  
pp. 16-22
Author(s):  
Shukla PK ◽  
Singh MP ◽  
Patel R
Keyword(s):  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Biological Applications ◽  
Plant Origin ◽  
Recent Past ◽  
Pharmacological Activities ◽  
Naturally Occurring ◽  
Recent Advances ◽  
Biological Aspects ◽  
Isatin Derivatives

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.

scholarly journals Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1258-1267 ◽  
Author(s):  
Hajime Ito ◽  
Eiji Yamamoto ◽  
Satoshi Maeda ◽  
Tetsuya Taketsugu
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Experimental Studies ◽  
Transition Metal Catalysts ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Nucleophilic Attack ◽  
Important Class ◽  
Mechanistic Studies ◽  
Induced Reaction

Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si–B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This boryl­ation reaction is further applied to the first direct dimesitylboryl (BMes2) substitution of aryl halides using Ph2MeSi–BMes2 and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials.1 Introduction2 Boryl Substitution of Organohalides with PhMe2Si–B(pin)/Alkoxy Bases3 Mechanistic Investigations4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi–BMes2/Na(O-t-Bu)6 Conclusion

ChemInform Abstract: L-Selectride-Mediated Highly Diastereoselective Asymmetric Reductive Aldol Reaction: Access to an Important Subunit for Bioactive Molecules.

ChemInform ◽  
2009 ◽  
Vol 40 (12) ◽  
Author(s):  
Arun K. Ghosh ◽  
Jorden Kass ◽  
David D. Anderson ◽  
Xiaoming Xu ◽  
Christine Marian
Keyword(s):  
Aldol Reaction ◽  
Bioactive Molecules ◽  
Reductive Aldol

ChemInform Abstract: Copper-ClickFerrophos-Complex-Catalyzed Enantioselective Reductive Aldol Reaction.

ChemInform ◽  
2009 ◽  
Vol 40 (39) ◽  
Author(s):  
Minoru Kato ◽  
Hiroshi Oki ◽  
Kenichi Ogata ◽  
Shin-ichi Fukuzawa
Keyword(s):  
Aldol Reaction ◽  
Reductive Aldol

Scope of the Reductive Aldol Reaction: Application to Aromatic Carbocycles and Heterocycles.

ChemInform ◽  
2004 ◽  
Vol 35 (13) ◽  
Author(s):  
Timothy J. Donohoe ◽  
David House ◽  
K. W. Ace
Keyword(s):  
Aldol Reaction ◽  
Reductive Aldol

ChemInform Abstract: Enantioselective Reductive Aldol Reaction Using Tertiary Amine as Hydride Donor.

ChemInform ◽  
2012 ◽  
Vol 43 (46) ◽  
pp. no-no
Author(s):  
Kazuki Osakama ◽  
Masaharu Sugiura ◽  
Makoto Nakajima ◽  
Shunsuke Kotani
Keyword(s):  
Tertiary Amine ◽  
Aldol Reaction ◽  
Reductive Aldol
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